


Cassie Got A Riddle

by DigitalSunburn



Category: Supernatural
Genre: Also joke and more riddles, Brother Love, Brothers, Crack, Destiel - Freeform, Fallen Angels, M/M, More - Freeform, Riddles, Sabriel - Freeform, come alive, fallen!cas, falling!gabriel, relationships, this time
Language: English
Status: Completed
Published: 2016-04-02
Updated: 2016-04-11
Packaged: 2018-05-30 20:11:43
Rating: General Audiences
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 2
Words: 2,550
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/6438556
Author URL: https://archiveofourown.org/users/DigitalSunburn/pseuds/DigitalSunburn
Summary: <blockquote class="userstuff">
              <p>What's a better time waster then riddles?<br/>See your favorite brothers in a car, with stupid riddles.</p>
            </blockquote>





	1. Chapter 1

"I have a good one!" I said to my older brother Gabriel. We have been in the car for hours, and my brother and I were telling riddles. We're heading up to see the Winchester brothers and Bobby. A new case had showed up and they need are help.

"What flower does everyone have on their face?" I asked, trying to keep my laugh from bursting out. 

Gabriel's eyes stayed on the road as he drove. I wasn't aloud to drive for obvious reasons. His lips thinned into a straight line as he frowned puzzled.

I smirked looking out the passenger window, watching as another farm went by. We were way out in the country.

Turning back to the shorter man I asked, "You give up?"

"Please, I never give up," He said thinking hard. Then his whiskey eyes sparkled

"I got it! Tulips! Two lips, right?" He asked bouncing in his seat. Car severing off the road before he corrected it.

"Right," I laughed happily, "Do you think Dean would like the riddle?" I asked fiddling with my hands

Gabriel rolled his eyes, "Of course!" 

My lips twitch upwards, "Good."


	2. So, A Horse Walks Into A bar

**Notes for the Chapter:**

> I do apologize for this terrible chapter.  
> I did actually have a good one, but my basement flooded and my laptop was on the floor.
> 
> Also I want to say thank you to Lily, who stupidly has belief in me that this chapter will be OK.

"I swear to dad, if you tell another riddle or joke I will drive my foot into this thing called your ass." Gabriel threatened as he crawled into their car and closed the door. 

They've been on the road for at least two and a half hours. They had just stopped so Castiel could use the washroom, even though the town they've been heading towards was only a few seconds away.  
But Castiel's had basically black mailed Gabe with his crush on Sam. He also threatened to tell Sam if they didn't pull over.  
Long story short, Gabriel just started the engine again.

The reason they've been driving is Castiel had lost his wings not to long ago, and Gabe was just starting to loss the ability to fly. Castiel's had told him just to fly to the Winchester's, but Gabe had refused to leave Cas alone for such a long period. That and the fact his driving skills need to be worked on.

Castiel glared at his brother, "I do not understand the need for such mean words." He huffed, "Expesily since you also made jokes." Shutting his door he joined his brother in his 1978 Lincoln Continental Mark V

"Yeah, but mine where at least worthy of being told." Gabriel sassed, snapping his fingers, a lollipop filled his mouth within seconds.

"Yours made no sense." The taller one sassed back.

"Fine, I have one that anyone human being or even monster would get.... So... a horse walks into a bar, right?" Gabriel started around the lollipop, as he drove down the road.

"Why would a horse walk into a bar?" Castiel asked his head resting on his window is confusion.

"To get a drink." Gabriel stated as it was obvious 

"It's a horse. He'd drink outside in a trough." He gestured out the window at the word 'outside'

Gabriel sighed as he took a left, down a narrow dirt road, "Well, this horse wanted something stronger."

Castiel straightened up in his seat as he saw the town sign. He turned to his older brother, "Horses don't drink alcohol."

"This one does." Gabriel bit his lollipop in half in frustration and then proceeded to eat the chunks

Castiel blinked confusion his set on his face, "And no one else in the bar is reacting to the fact that a horse walked in?"

Blinking rapidly Gabriel turned to his brother, "Yeah. Alright yeah, a couple of people react," His eyes went back to the road as he took a right turn. 

"They're surprised, but then they get over it." Gabriel sighs hands flying everywhere, but yet somehow he still keeps the vehicle in the lines, "The horse walks up to the bartender as says, -'Hey, I would like a jack and coke'-"

"Wait!" Castiel interrupts even more confused, "Now the horse can talk?"

Gabriel puts his head down as he sighs clearly frustrated, he pause for a few seconds before continuing, "Can I just finish my joke?" He asked

Castiel takes a sip a his water bottle, "Let me tell you one." He says, knowing his brother will let him. The last time Gabriel told him no to anything, Dean was all up in his personal space, threatening him.

Gabriel threw his hands up, "Go ahead." Anger laced his voice, but Castiel knew it was just for extra dramatic effect

Castiel smiles, "knock knock."

Gabriel rolled his eyes, fondness expression has taken over the angry one, "Who's there."

"We where supposed to turn back there." Castiel said pointing behind them, as the road mark, 'St. Hume Street.' 

Gabriel glared at the taller man, "Funny." He pulled the car into a random driveway and turned around and drove down the right road.

Silence filled the car, as Castiel counted how many reds cars passed. 

"We're about to reach then ten minutes to the motel marker you insisted that I put up." Gabriel announce, rolling his eyes when he only got a hum in response.

"What has roots as nobody sees, is taller than trees. Up, up it goes. And yet never grows?" Gabriel asked, growing uncomfortable by the silence.

"Mountain... It's one of the riddles from the Hobbit.. You'll have to try harder."

Gabriel looked shocked at the fact Cas had gotten it, "You read the Hobbit?"

Castiel threw him one of his infamous 'bitch please' looks that Sam had taught him, "I've seen the movies too. Dean make me watch all of them. Of course he fell asleep half way into the first one." Cas smile at the memory of Dean's head on his shoulder. His freckles lite up under the orange motel light. His mouth opened as his alcohol breath blow on his neck.... Castiel's hand came up to his neck, as he felt a puff of air. 

Castiel frowned at the sudden warmth on his neck. He turned to his left to see Gabriel looking up at him. Lips in an 'o' shape as he exhaled. Cas shot a death glare at his brother. Gabriel retreated with his hands up in surrender 

"Forgot I can still reads minds huh? Cassie-face." Gabriel smirk as he snaped his fingers and the vehicle coming back into his control, "It's OK Cassie, I forgive you for the death glare."

Castiel opened his mouth to say something, when a cherry flavored lollipop, popped into his mouth. He shook his head as he took it out and licked it.

"Anymore riddles?" Cas asked as he look at the stars. It was around midnight and the moon was shining in the blackish, purplish sky.

Gabriel gave him, his, bitch face, "Of course. Let's see... Gosh, no that's so bad. How could I? Worst person alive. Half person, half Angel I guess.... Oh yes, what is greater than God, more evil than the Devil, the poor have it, the rich need it, and if you eat it, you'll die?"

"Nothings greater then Dad. And I mean Cain's evil, but not as evil as Lucifer, there for nothing can be more evil than him. And the rest of the riddle answers it self. Nothing." Castiel answered, looking out the front window. The red from the stop light, glowed on his face. Lightning up his face and showing off his just a tad to skinny check bones.

Gabriel clicked his tongue as he winked at the taller one, "Yes, sir-" the rest of the sentence was cut off as a loud band came from the hood of the car. Both brothers tensed up as Angel blades fell from Gabe right sleeve. Cas quickly reached under his seat and grabbed his.

The hood creaked as something crawled across it. Gabriel looked into his brothers eyes, taking back as he saw fear in them.  
Something he's never seen before. It broke his heart. He let out a breath as he watch the color red turn to green on Castiel's face. He quickly grabbed ahold of the steering wheel and pressed on the gass. Not stopping till they reached the motel, two blocks away.

Once the car was park and turned off. Both brothers let out a nervous laugh as they leaned against their seats with their eyes closed. All a sudden a knock came from Cas's window scaring them. 

"Hey, you guys OK?" Came a grumpy voice. The brother smiled as they looked over and saw Bobby. Quickly they both jumped out of the car and Gabriel pressed himself against the older hunter.

Gabriel smiled, "Of course why wouldn't we be." He asked.

"I'm sorry Bobby. A few blocks down the road, something had jumped on our hood. Scared us." Cas explained walking beside the hunter as he struggled with walking to the door, with a semi ex-archangel on his side.

"Did you get a good look?" He asked, unlocking the door to his motel room.

Cas shook his head, "No, sir."

Bobby sighed, "How many times do I need to tell you? Call me Bobby." 

Gabriel smirk, "Yeah, Cas! Call him Bobby!"

Cas stuck his tongue out at his brother, instantly regretting it as another lollipop filled his mouth. Cas growled walking closer to the shorter man. 

"Boys!" Bobby yelled, breaking them apart, "Sam and Dean are in room, 120. Go make yourself useful." He said walking to the washroom and closing it.

Gabriel and Castiel shugged as they made their way down the lot. Confused as to why the rooms where so far apart.

Once they reached the door, it opened up to Dean with his gun out (An actual gun, you perver) and Sam with his Demon Blade out (That wasn't much better, was it?) 

Gabriel raised his eyebrows, amused. And Castiel, well Castiel stills stuck on the, 'dean has his gun out' part.

No, Castiel looked unimpressed, "You can put that away now Dean."

Dean blinked, taking a second to realize what Cas meant, "Oh, yeah. Duh." He turned on the safety and threw it on one of the beds. As Sam set his blade on the stand beside the door.

"Gabe, Cas," The tallest one greeted, moving to the side and letting them in, "I hope the trip wasn't to bad."

"Nah," Gabe said plopping down on the sofa in front of the T.V. "It was rather fun, I mean as fun as it could be with a human." He joked

"Hey," Dean warned sitting on his bed, as Cas was standing beside him, "Be nice to Cas."

Gabe rolled his eyes, making room for Sam on the sofa. Once Sam got comfy, Gabriel stretched out placing his head on Sam's lap. Sam's hand instantly went to play with Gabe's hair.

Cas smiled at the sight of his brother and Sam. He then turned to Dean, only to find him staring at him.

Clearing his throat, Dean spoke, "So, the reason you're here is because we got a skinwalker."

Gabe sat up, wincing as Sam's hair got stuck in one of his curly locks, "I bet that's what attacked us."

Dean sat up, "What do you mean attacked you?" His eyes scanned both brothers, trying to fine cuts. He knew Gabe would of healed them as much as he could, but sometimes it wasn't enough.

"Gabriel means, what attacked my car." Cas explained resting his hand on Dean's should in a calming jester.

"I guess you guys didn't get a good enough look." Sam sighed, running his hand through his hair and sat down on his bed, "Well there's not much we can do tonight. I suggest we turn in."

Cas nodded as he threw himself on the small sofa, wincing as he landed. Gabe sat on the floor, knowing once everyone was asleep he'd sleep as well.

"Actually Cas," Said Dean from the end of the sofa, Castiel's dirty socks rested on his stomach "I thought it would be to crowed, and the sofas not comfy.. I- I went a head and got us a separate room...Once small problem though... It- We have to sh- there's only one bed." Dean stuttered, "I hope you don't mind. It was last minute."

Cas smiled as he got up from the Sofa and made his way to Dean, "Thank you Dean." He said. He blushed shyly when he heard Sam's snickering or Gabe's cat calls

"I'll go get my bags," Cas said walking towards to door. 

"I'll come with." Dean said, a little to quickly, "I mean, there's a monster out their and I don't want you to get hurt. Besides it's dark, and you might trip, or maybe get hit on my a stripper. I know you social skills are that great yet-" Dean's sentence was cut off by a pair of lips.

Dean touched Castiel's face carefully, as if Cas would realize what he was doing and regret it. But Cas just pulled him closer, his fingers clutching Dean's shirt. 

Castiel's tongue pushed past Dean's lips and met his tongue. Within seconds both tongues danced together sloppily. Dean moaned as Cas sucked on his tongue.  
As he's pressing his whole body against Dean's. 

We they finally parted Cas whispered, "Do you ever stop talking?"

Dean laughed as he rested his forehead against Cas's, "Never. Especially in bed."

Castiel's moaned at the information, "Let's go get my stuff and head to your room."

Dean nodded, stepping out of Castiel's personal space and turned around -and to Dean's horror- saw Sam and Gabe were sitting on each bed with smirks on their face. Dean had totally forgotten about them.

"I've never seen someone's boner go down that fast," Gabe grinned patting Dean on the back, "At least not because of me."

Dean and Cas rolled their eyes as they headed out the door. Dean paused and looked back at the other two, "Oh, don't forget to use protection." He smiled, leaving th two blushing, with mouths open in an 'o' shape. And to Sam's horror, Gabriel yelled

"I'm still an Archangel! I don't need protection." 

 

(BONUS SABRIEL)

"Hey. A horse walks into a bar." Gabriel said grinning as he pulled back from Sam's embrace as they laid on the bed. 

Sam paused, a confused expression took over his love bird one. His eyebrows formed a thin line across his forehead as he asked, "Why would a horse walk into a bar?"

Gabriel closed his eyes and let out probably the biggest sigh of the day, as Castiel spoke from the doorway of the motel. Having catch their convention as him and Dean walk passed them on their way to Dean's motel room, "You think that's bad, it talks, too." Giving a sympathy smile to Sam, as Dean practically pulled him away and down the lot. Probably to do the nasty.

(BONUS> THE JOKE GABRIEL WAS GOING TO TELL BUT THOUGHT IT WAS TO MEAN)

"Anymore riddles?" Cas asked as he look at the stars. It was around midnight and the moon was shining in the blackish, purplish sky.

Gabriel gave him, his best bitch face, "I have one, but it's not really a riddle. More of a joke... What did one orphan say to the other?"

Castiel shrugged, "I don't know."

"Where's the pie!"

**Notes for the Chapter:**

> If you see this it mean you've stuck around till the end. And I apologize for the last joke, I'm a horrid person.

**Author's Note:**

> Comments are very much welcomes.  
> Tell me if you want another chapter, with a bit of Sabriel and Destiel, and of course Bobby!!


End file.
